Diphenylchlorphosphat
Diphenyl chlorophosphate
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Grundinformationen
- CAS
2524-64-3- Standard-SMILES
O=P(Cl)(Oc1ccccc1)Oc1ccccc1- InChIKey
BHIIGRBMZRSDRI-UHFFFAOYSA-N- Summenformel
- C12H10ClO3P
- Durchschnittliche Molmasse
- 268,63 g/mol
- Monoisotopische Masse
- 268,00560849
Überblick
Diphenyl chlorophosphate appears as a clear colorless to light yellow liquid with a pungent odor. Insoluble in water and denser than water. Hence sinks in water. Contact may severely irritate skin, eyes and mucous membranes.
Namen und Bezeichner
- Bevorzugter Name
- Diphenyl chlorophosphate
- IUPAC
- [chloro(phenoxy)phosphoryl]oxybenzene
- Lokaler Name
- Diphenylchlorphosphat
- Englischer Name
- Diphenyl chlorophosphate
- Summenformel
- C12H10ClO3P
- Molmasse
- 268.63
Namen und Synonyme
Diphenyl chlorophosphate2524-64-3Diphenyl phosphorochloridatediphenyl chlorophosphonateDiphenylphosphoryl chlorideChlorodiphenoxyphosphine oxidePhosphorochloridic acid, diphenyl esterDiphenoxychlorophosphine oxideO,O-Diphenyl chlorophosphateDiphenylphosphoric acid monochlorideDiphenyl phosphochloridatePhosphoric acid chloride diphenyl ester
Weitere Namen anzeigen
DPCPCHLOROPHOSPHORIC ACID DIPHENYL ESTERDPOCDiphenylchlorophosphonateDiphenyl chloridophosphateDCP:DPCP(PhO)2POCIAURORA KA-1636
DiphenylphosphorylchloridateDTXSID2044892Phenyl phosphorochloridate ((PhO)2ClPO)1KEE9757OTNSC-43771DIPHENYL PHOSPHOROCHLORATEDTXCID0024892PHENYL PHOSPHOROCHLORIDITE
Datenbank-Bezeichner
- CAS
2524-64-3- PubChem CID
- 75654
- DTXSID
DTXSID2044892- ChEMBL
CHEMBL3188224- UNII
- 1KEE9757OT
- EC Number
- 219-759-6
- Nikkaji
- J7.599J
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 3,5
- Polarare Oberfläche (TPSA)
- 35,5 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 17
- Formalladung
- 0
- Komplexität
- 249
Experimentelle und physikochemische Eigenschaften
Density1.296 @25 °C
Physical Description
Diphenyl chlorophosphate appears as a clear colorless to light yellow liquid with a pungent odor. Insoluble in water and denser than water. Hence sinks in water. Contact may severely irritate skin, eyes and mucous membranes.
Liquid
Physikochemische Eigenschaften
- Siedepunkt
- 314 · 314-316 °C/272 mmHg (lit.)
- Dichte
- 1.296 g/mL · 1.296 g/mL at 25 °C (lit.)
- Dampfdruck
- 10 mm · 10 mm Hg ( 190 °C)
- Brechungsindex
- 20 · n20/D 1.55(lit.)
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- 2 · Inert atmosphere,2-8°C
- Löslichkeit
- Chloroform (Slightly), DMSO (Slightly)
- Aggregatzustand
- Liquid
- Farbe
- Clear colorless to light yellow
- Wasserlöslichkeit
- MAY DECOMPOSE
- BRN
- 654130 · 654130
- Henry's Law Constant
- 3.7 · 3.7×10-2 mol/(m3Pa) at 25℃, Bartelt-Hunt et al. (2008)
- Stabilität
- Stable under recommended storage conditions., Stable Under Recommended Storage C
- InChI
- 1S/C12H10ClO3P/c13-17(14,15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
- InChIKey
- BHIIGRBMZRSDRI-UHFFFAOYSA-N
- SMILES
- ClP(=O)(Oc1ccccc1)Oc2ccccc2
- CAS Datenbank
- 2524 · 2524-64-3(CAS DataBase Reference)
- NIST chemische Informationen
- Diphenyl chlorophosphate(2524-64-3)
- EPA chemische Informationen
- Phosphorochloridic acid, diphenyl ester (2524-64-3)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H302 (69.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 166 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: Phosphorochloridic acid, diphenyl ester
Phosphorochloridic acid, diphenyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphorochloridic acid, diphenyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 08-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19780
Diphenyl phosphorochloridate: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelCorrosive
Fire HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity Profile
DIPHENYL CHLOROPHOSPHATE is incompatible with bases (including amines) strong oxidizing agents, and alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. May form highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (69.9%)
Sicherheit und Schutzausrüstung
Fire FightingExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Protective Action Criteria (PAC)
7.9 [mg/m3]
87 [mg/m3]
520 [mg/m3]
Personal Protective Equipment (PPE)Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3265 8/PG 2
- hs_code
- 29209085
- risk_code
- 34-37
- hazard_code
- C
- safety_code
- 26-36/37/39-45-7-24/25-23
- hazard_class
- 8
- packing_group
- III
- Speicherklasse
- 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Corr. 1B
Chemie und Industrie
Verwendung und Herstellung
U.S. Production2023: 1,000,000 - <5,000,000 lb
Consumer UsesIntermediate
Industry UsesHydraulic fluids
General Manufacturing Information
Utilities
Phosphorochloridic acid, diphenyl ester: ACTIVE
Anwendungen
VerwendenDiphenyl chlorophosphate is used to prepare cyclohexyl-amidophosphoric acid diphenyl ester by reacting with cyclohexylamine. It is also used in the synthesis of alfa-substituted beta-lactams, anhydrides, esters and thioesters. It is also employed in the conversion of aldoximes to nitriles. Further, it is used in the preparation and reaction of enol phosphates, guanosine-adenosine-5',5'-triphosphate, guanosine-cytidine-5',5'-triphosphate, guanosine-uridine-5',5'-triphosphate, diguanosine-5',5'-diphosphate and diguanosine-5',5'-triphosphate. In addition to this, it serves as a phosphorylating agent for the preparation of 2-deoxy-D-galactose-3 and -6 phosphoric acids.
Darstellung
synthetischeThe preparation of Diphenyl chlorophosphate is as follows:With a thermometer,Reflux condenser and mechanical agitation120 g of dichloromethane was placed in a 500 ml four-neck reaction flask.7.3 g of N,N-dimethylformamide,Stirring temperature control below 10 °C,Put 28g of bis(trichloromethyl) carbonate,A solution of 50 g of diphenyl phosphate and 120 g of dichloromethane was added.After the addition, the reaction was carried out for 3 hours. After the end of the reaction, the temperature was controlled below 10 ° C, 20 g of water was slowly added, and the mixture was stirred and the organic phase was dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the filtrate was evaporated under normal pressure. The temperature was lowered to 0 ° C, and the insoluble matter was removed by filtration to obtain 48.9 g of diphenyl chlorophosphate. The purity of GC was 99.2%, and the yield was 90.3%.
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